James Flack Norris Award In Physical Organic Chemistry

Sponsored by the ACS Northeastern Section

Dennis A. Dougherty, George Grant Hoag Professor of Chemistry at California Institute of Technology and lifelong baseball fan, is honored for a triple play in physical organic chemistry. His body of work spans high-spin polyradicals and materials, molecular recognition, and chemical neurobiology.

Dougherty "has an uncanny ability to uncover fundamentally new principles in the areas that he investigates and rapidly establishes himself as a world leader in these areas," remarks Eric V. Anslyn, Norman Hackerman Professor of Chemistry at the University of Texas, Austin.

Dougherty, 55, received bachelor's and master's degrees from Bucknell University in 1974. He earned a Ph.D. with Kurt Mislow at Princeton University in 1978 and completed a postdoctoral fellowship with Jerome A. Berson at Yale University. He joined the faculty at Caltech in 1979 and has taught there ever since. "I have been very fortunate to work with fantastic students and to have the support of great colleagues at Caltech," Dougherty says.

At the start of his independent career, Dougherty synthesized and characterized high-spin molecules and polymers. These materials find use as organic magnets, which might be useful in high-density optical data storage systems and other applications.

He then moved into molecular recognition, where he found that the interaction between a cation and the face of an aromatic ring could motivate noncovalent binding in aqueous solutions. This phenomenon, which Dougherty termed the cation-π interaction, was a new intermolecular force that today is mentioned alongside classic forces such as hydrogen bonding, Anslyn says. "It is hard to imagine a greater contribution to such a large and encompassing field as molecular recognition than that of discovering a new binding force."

The cation-π interaction also has biological implications, as Dougherty was quick to realize. He studied its role in binding interactions between cationic and aromatic amino acids in proteins and correctly predicted that the neurotransmitter acetylcholine uses the cation-π interaction to bind its receptor. That work led him to make the transition to chemical neurobiology, where his collaborations with Caltech neurobiologist Henry A. Lester have illuminated the relationship between structure and function in ion channels. For example, he showed that isomerization of a key proline residue acts as the hinge in a neurotransmitter-gated ion channel (C&EN, Oct. 2, 2006, page 44). This work "delivered a breakthrough in chemical signaling mechanisms," says Julius Rebek Jr., director of the Skaggs Institute for Chemical Biology and professor of chemistry at Scripps Research Institute.

Dougherty "has shown that even in an extraordinarily complex area like neuroscience, the tools of physical organic chemistry can produce important results," says Kendall N. Houk, distinguished professor of chemistry at the University of California, Los Angeles.

Dougherty will present the award address before the Division of Organic Chemistry.